Leaning In

Trademark Property

Leaning In is a podcast exploring the future of mixed-use real estate. Trademark Property Company CEO Terry Montesi, and other executives, speak with experts from various backgrounds and areas to discuss mixed-use, multifamily, and brick-and-mortar retail, and what it looks like to lean into it while others are leaning out. For more information about Trademark, visit www.trademarkproperty.com

  1. 11/20/2025

    From Dallas to Washington: Ray Washburne on Real Estate, Leadership, and Legacy

    Ray Washburne joins host Terry Montesi on Leaning In for an in depth conversation about real estate, leadership, and the evolving landscape of Dallas. Ray reflects on his early entrepreneurial years, the lessons that shaped his investment approach, and the principles that guide his work across sectors from hospitality to mixed use development. He and Terry dive into the transformation of Highland Park Village, the challenges and opportunities within downtown Dallas, and the broader economic signals influencing commercial real estate today. They discuss: Ray’s early path into real estate and the mindset shaped by growing up in DallasThe strategy behind acquiring and revitalizing Highland Park VillageWhy reputation and long term relationships drive success in Dallas and WashingtonThe future of downtown Dallas and major projects that could reshape the cityHow consumer behavior, construction costs, and AI are influencing the real estate cycleChallenges in office, adaptive reuse, and where new opportunities may emergeLinks: Gillon Property Group Trademark Property Terry on LinkedIn Audio Topics (00:00:00) - Intro(00:01:25) - Ray’s career and background(00:04:38) - Leadership philosophy(00:09:23) - Luxury retail and Highland Park Village(00:20:48) - Challenges and future of Dallas real estate(00:23:44) - Downtown Dallas development and vision(00:32:12) - Incentivizing real estate investment(00:36:35) - Shifts in domestic manufacturing and tariffs(00:38:17) - Challenges in real estate development(00:41:19) - Office space and adaptive reuse strategies(00:44:34) - Institutional real estate investment trends(00:49:43) - Creating unique experiences in real estate(00:52:55) - Lessons from public sector experience(00:58:30) - Advice for young real estate professionals

    1h 2m

  2. 10/13/2025

    Navigating Retail Real Estate: Insights from Kimco CEO Conor Flynn

    In this episode of Leaning In, host Terry Montesi sits down with Conor Flynn, CEO of Kimco Realty, for an in-depth discussion about the evolution of retail real estate, the future of mixed-use development, and the trends shaping consumer behavior. Conor shares lessons from his two decades at Kimco, detailing the company’s strategic shift toward grocery-anchored shopping centers, its multifamily expansion efforts, and the advantages of scale in today’s REIT landscape. The conversation also explores how technology, capital markets, and macroeconomic uncertainty are influencing decisions across the retail and development sectors. They discuss: • Lessons learned from a career built within Kimco Realty • How grocery-anchored centers became the foundation of Kimco’s portfolio • The company’s multifamily strategy and use of joint venture partnerships • Navigating today’s capital markets and managing risk amid uncertainty • Emerging retail trends, from off-price and grocery to health and wellness • How technology and consumer behavior will shape the next generation of shopping centers Links: Trademark Property Terry on LinkedIn Kimco Realty Conor on LinkedIn Topics: (00:00:00) - Intro (00:01:13) - Connor Flynn's journey at Kimco (00:04:09) - Lessons learned in real estate (00:07:44) - Kimco's strategic position and mission (00:15:03) - Multifamily expansion and redevelopment (00:18:07) - Navigating economic uncertainty (00:26:10) - Building for a 300 spread (00:26:30) - Navigating uncertainty in development (00:27:50) - Institutional partnerships and success stories (00:29:29) - Retailer categories and trends (00:30:51) - Grocery anchors and leasing strategies (00:39:04) - National vs. local tenants (00:40:42) - Future of retail real estate (00:45:13) - Advice for young professionals (00:46:57) - Conclusion and final thoughts

    48 min
  3. AI's Influence: Transforming Human Behavior and Retail Dynamics

    07/17/2025

    AI's Influence: Transforming Human Behavior and Retail Dynamics

    In this forward-looking episode of Leaning In, Terry Montesi is joined by Bart Higgins and Katie Hillier of Future Perfect X, to explore how artificial intelligence is transforming the future of human behavior, retail, and placemaking. Drawing on their deep backgrounds in design, anthropology, and innovation, Bart and Katie unpack how AI will shift the foundational drivers of consumer experience and commercial real estate. From programmable biology and co-intelligent AI agents to personalized retail journeys and ambient environments, they illustrate what it means to future-proof a business in the age of the "limitless self." This conversation challenges leaders to rethink how places are designed and how brands will maintain emotional relevance in an AI-mediated world. They discuss: Why understanding the future human is more important than understanding the technology itselfHow AI will alter core human traits like identity, emotion, and decision-makingWhy the commercial construct of retail must evolve beyond the needs-based and self-growth economiesWhat the rise of avatars and AI companions means for brand loyalty and physical retailHow retail developers can position themselves as tastemakers in a world of infinite contentThis episode is a must-listen for anyone shaping the future of consumer spaces, brands, or experiences. Topics: (00:00:00) - Intro(00:00:42) - Introducing Bart and Katie(00:04:00) - How does one go about being an innovation consultant?(00:12:34) - How brands and businesses in CRE can future-proof themselves(00:16:19) - How will AI disrupt retail as a business model?(00:23:05) - How is the retail experience going to change as we move forward?(00:27:59) - What are some of the needs consumers are expecting retailers to fill?(00:42:05) - How do you see AI impacting how retail places need to evolve?(00:48:03) - What does the future of retail look like outside of AI?(00:50:36) - Who’s doing a great job of future-proofing themselves?(00:53:53) - Closing questions

    1h 2m
  4. The Art of Retail Reinvention: A Conversation with RH’s Steve Rouman

    06/25/2025

    The Art of Retail Reinvention: A Conversation with RH’s Steve Rouman

    In this episode of Leaning In, Trademark CEO Terry Montesi sits down with Steve Rouman, SVP of Real Estate at RH, to talk about his journey from the landlord side of the business to leading real estate strategy for one of retail’s most design-driven brands. They dive into RH’s transformation into a luxury lifestyle brand, the future of retail site selection, post-COVID consumer behavior, and how physical retail and e-commerce can work together. Steve also shares advice for industry newcomers and why human connection still sits at the heart of retail. 🎧 Listen in for a forward-looking take on retail, design, and the evolving role of place. Topics: (00:00:00) - Intro (00:01:12) - Steve’s background and career (00:08:05) - RH's transformation and real estate strategy (00:13:11) - Site selection and unique real estate moves (00:18:02) - Surprises and lessons in retail site selection (00:26:12) - Future growth and expansion plans (00:30:07) - New store concepts and expansions (00:32:40) - AI and the future of retail (00:35:29) - E-commerce and physical retail synergy (00:39:09) - Retailers excelling in brick and mortar (00:44:07) - Future of retail real estate (00:49:24) - Advice for aspiring retail real estate professionals (00:53:13) -Terry’s proudest moments (00:58:05) - Conclusion and final thoughts Links: Trademark Property⁠ ⁠⁠⁠⁠⁠Terry on LinkedIn RH Steve on LinkedIn

    59 min

  5. 05/30/2025

    Boom, Bust, or Balancing Act? 2025's Economic Outlook

    In this special live episode of Leaning In, Trademark CEO Terry Montesi is joined by returning guest and renowned economist Dr. Peter Linneman to break down what’s shaping the economic landscape as we move through 2025. From inflation and interest rates to capital flows, consumer shifts, and real estate dynamics, Peter offers grounded insights and a healthy dose of perspective on where we’ve been—and where we may be headed. Whether you're navigating strategy in retail, real estate, or simply trying to make sense of a volatile market, this conversation delivers clarity, not noise. 🎧 Stream now and follow Leaning In for more conversations on what’s shaping the future of commercial real estate.

    1 hr

  6. 04/15/2025

    Open-Air Retail, Supply-Demand Trends, and What’s Next with DLC's Adam Ifshin

    The retail real estate landscape is evolving, and few people understand its intricacies better than Adam Ifshin, Founder and CEO of DLC Management. In this episode, Trademark CEO Terry Montesi sits down with Adam to discuss how value-driven open-air centers, omnichannel innovation, and institutional capital are reshaping the industry. Adam shares insights on why open-air retail continues to outperform, how AI is poised to revolutionize retail operations, and why institutional investors are re-embracing retail real estate. He also dives into the impact of supply and demand dynamics, the future of apparel shopping, and the challenges of new development in today’s market. With over 30 years of experience and a track record of transforming underperforming assets, Adam’s perspective offers a must-listen deep dive into where retail and retail real estate are headed. To stay informed and hear more from top voices in the industry, subscribe to Leaning In and sign up here to be the first to know when a new episode drops! Links: ⁠Trademark Property⁠ ⁠⁠⁠⁠⁠Terry on LinkedIn Adam on LinkedIn Topics: (00:05:22) - DLC's Evolution and Core Values  (00:11:48) - Investment Strategy and Market Trends  (00:16:09) - Pandemic Impact on Retail  (00:22:39) - Omnichannel Retail and Future Outlook  (00:24:43) - Retailers Must Adapt or Perish  (00:25:35) - Bankruptcy and Replacement Tenants  (00:27:31) - The Shift to Open-Air Retail  (00:30:40) - Consumer Behavior Post-Pandemic  (00:32:46) - Interest Rates and Inflation Impact  (00:36:31) - Supply and Demand in Retail Real Estate  (00:43:23) - The Role of AI in Retail Real Estate  (00:45:52) - Future Trends in Retail Real Estate  (00:51:04) - Closing Remarks and Final Thoughts

    52 min

  7. 03/21/2025

    Retail’s Evolution: Malls, Department Stores, and the Road Ahead

    The retail world is changing, and two of the biggest names in department stores—Dillard’s and Macy's—are at the forefront. In this episode, Trademark CEO Terry Montesi sits down with the SVPs of Real Estate: Chris Johnson of Dillard's and Chuck DiGiovanna of Macy's, to discuss Retail’s Evolution: Malls, Department Stores, and the Road Ahead. These industry giants share insights into how department stores and malls are adapting to today’s retail landscape, from innovative strategies to the importance of creativity and strong developers. Chris and Chuck also explore the impact of technology, capital markets, and tariffs on the future of retail. With their extensive experience at some of the most recognizable names in retail, this episode is a must-listen for anyone interested in the future of malls, department stores, and the retail industry as a whole. To stay informed and hear from two leaders shaping the future of retail, subscribe to Leaning In and sign up here to be the first to know when a new episode drops! Links: Trademark Property ⁠⁠Terry on LinkedIn Chris on LinkedIn Chuck on LinkedIn Topics: (00:00:00) - Intro(00:01:01) - Chuck and Chris' Journey in Real Estate  (00:02:31) - Current State of Macy's and Dillard's  (00:03:49) - Challenges and Trends in Retail  (00:05:53) - The Future of Malls and Department Stores  (00:09:22) - Investment and Redevelopment Opportunities  (00:16:18) - The Role of Department Stores Moving Forward  (00:24:25) - Navigating Mall Usage Restrictions  (00:25:59) - Impact of the Pandemic on Retail  (00:29:23) - The Future of Online and Brick-and-Mortar Stores  (00:33:07) - Advice for Mall Property Owners  (00:37:08) - Challenges in Mall Financing  (00:43:37) - Future Trends in Retail and Real Estate  (00:47:24) - Closing Thoughts and Opportunities

    49 min
  8. Celebrating 20 Years of Creating Community at Market Street Woodlands

    01/09/2025

    Celebrating 20 Years of Creating Community at Market Street Woodlands

    Uncover the story behind one of Texas' most innovative mixed-use developments: Market Street - The Woodlands.  In this episode of Leaning In, we revisit the groundbreaking opening of Market Street in The Woodlands, Texas—one of the nation’s first mixed-use town center projects. Join Trademark Founder & CEO Terry Montesi and Managing Director & CIO Tommy Miller as they share the story behind this visionary development and its lasting impact on the retail real estate industry in Houston and beyond.  Stay connected with real estate trends and inspiring stories from industry leaders by subscribing to Leaning In. Links: Trademark Property Terry on LinkedIn Tommy on LinkedIn Market Street – The Woodlands Topics: (00:00:00) - Intro (00:01:00) - The story behind Market Street Woodlands (00:06:27) - The development and design process (00:13:18) - Leaps of faith in closing the deal and leasing momentum (00:17:41) - How have we maintained success over 20 years of retail evolution? (00:29:19) - How do you hope visitors feel about the space? (00:30:52) - What do you hope for the future of the property?

    35 min
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4.8
out of 5
20 Ratings

About

Leaning In is a podcast exploring the future of mixed-use real estate. Trademark Property Company CEO Terry Montesi, and other executives, speak with experts from various backgrounds and areas to discuss mixed-use, multifamily, and brick-and-mortar retail, and what it looks like to lean into it while others are leaning out. For more information about Trademark, visit www.trademarkproperty.com

Information

  • Creator
    Trademark Property
  • Years Active
    2020 - 2025
  • Episodes
    82
  • Rating
    Clean
  • Copyright
    © Trademark Property
  • Show Website
    Leaning In